We were in bed, still catching our breath, when she looked at me with that soft smile she always got afterward. She was thirty, I was twenty-two, and we’d met online a few weeks earlier. She’d driven out to me for our first date, bringing food and a movie, and I didn’t think much of it. But then it became a pattern.
She’d come to me every time, never asking me to drive to her. She’d show up with gifts, tickets to sports games, whatever she thought I might like. I couldn’t match her. I was broke, working a simple job and serving in the National Guard.
I told her I felt bad about it, that I wished I could take her places and buy her things. She just smiled and said she didn’t care about any of that. She only cared about seeing me. When what happened next happened, I got scared I’d messed everything up.
For a week she didn’t contact me. I figured the connection we had was gone. Then she texted, apologizing for the silence, explaining her job had taken her somewhere without reliable communication. I didn’t care about the details.
She was back. Eventually I asked what she did for a living. Turned out she was the CEO of a multi-million-dollar firm. My heart nearly stopped.
I wanted to ask why she’d want anything to do with me, but I didn’t. For three years we kept seeing each other. Every time she brought food and we fell into bed together, and it was the best sex I’d ever had. Then she invited me camping and introduced me to her entire family.
They were the nicest people I’d ever met, rich in a way you could see just by looking at them, and none of them ever judged me. They bought me a brand-new vehicle. They bought me a house. They got me a high-paying job.
It couldn’t get any better. But it did. She told me she loved me, and I realized I’d been in love with her all along. We made it official.
Nine months now, with a kid on the way. Finally something I can contribute to. I used to spend all my time on MMOs, especially Guild Wars 2. I got friendly with everyone in my guild, including a married couple who were about ten years older than me.
They seemed fine at first, but eventually they broke up. He was controlling, an asshole to her in ways that were starting to show in his guild chat humor. She was the only one online at three in the morning one night, and we ended up talking longer than we ever had before. I was just trying to comfort her.
I’d also recently become single, so we were drawn to each other. She visited my city for a week and asked me to show her around. I was a college student, so I planned things within my budget, but she kept convincing me to try more expensive stuff and covering everything. She thanked me for being there, for making her feel less lonely.
It felt strange. I didn’t want to feel like a gold digger. But she reassured me it was fine, and we had a lot of sex in a really nice hotel suite, ate at restaurants way out of my price range, went clubbing. It was an eventful week.
We both agreed nothing was serious, we were just enjoying the moment. She flew back. Life went on. We got busy, stopped playing online as much, and our communication faded.
It’s been years since we last spoke. I still hope she’s doing well. I’ve been working at a restaurant for over a year and a half. This elderly couple comes in at least three times a week.
They’re both in their seventies. She’s always in fur coats with different jewelry, but she’s losing herself to age. Not full dementia yet, but not quite all there. He leads her around, walks her to their regular booth, helps her order.
I found out recently he lives in his car. She pays for him to have a few meals with her each week in exchange for companionship. It’s kind of a weird elderly escort deal. Sad, but also sweet in a strange way.
He’s protective of her, genuinely cares. He keeps all her receipts, makes sure she gets exactly what she wants, especially her one and a half scoops of vanilla ice cream for dessert. How he survives Minnesota winters living mostly in his car is probably purely thanks to her. When I was nineteen, I met a thirty-year-old widow named Hans.
She said she played games to pass the day because she was financially set for life after her husband passed and wanted to make some friends. We started playing more and more until I couldn’t keep up because my controller and headset broke. She asked for my address, and a week later I had a brand-new controller and headset. I thanked her and asked what I could do in return.
She said just keep playing with her. Over the next few years she’d occasionally buy me new games when they came out, even collector’s editions. Eventually we drifted apart because I couldn’t find time to play with school and work. I still miss her and try to find her online sometimes, but I can’t remember her gamertag.
She’ll always be one of my best gaming buddies. In my early twenties I met a woman in a bar, mid-forties, drinking alone. I stood next to her to order a drink, and she leaned over, complimenting my body. I said thanks and told her she looked great too.
She gave me her business card and told me to text her around two a. m. I did. She rolled up in a super-nice Benz, we went back to my place, and in the morning she was gone.
The next weekend she texted, told me to wear a dress and be there at eight, to clear my whole weekend. I did. She had a huge eight-bedroom house. She taught me things I didn’t even know I was interested in.
The next weekend she showed up with high-end clothes and shoes for me, plus kinky toys for me to use on her. She made me into a half-assed Dom, and I’d tie her up and do just about anything I wanted. We had a good time. Then she fell off the face of the earth.
I don’t regret it one bit. She spoiled the hell out of me, made me food, brought it to me in bed, massaged my body almost every day. She slept in a different room. Between the sexual times we had long conversations about everything.
I was seeing a coworker for about two months, ten years my senior. We’d always exchanged certain looks over the year, but she was going through a divorce with a well-to-do architect. We’d bonded over our depressive situations. Nothing happened until I handed in my resignation and told everyone I was moving states.
She suggested we get a drink one night. Nothing happened. Then she invited me to her place. She had three awesome kids, an open bar of anything I wanted, amazing cooking.
We bonded in the bedroom too. It was almost perfect, except I sneaked out at dawn before the kids woke up. This went on for about seven weeks. Then I had my car packed, ready to go.
We spent one last night together. We said our goodbyes, and I drove off. Last I heard from her, as per her arrangement and her request. It could have worked out.
A couple of years ago I was home from college on break, matched with a girl on Tinder. We texted for three days and decided to meet for sushi. She came to my house first, parked outside for fifteen minutes, texted that she was too shy to come in. Eventually she walked up.
We had sushi, went back to my place, and one thing led to another. She stayed the night. We got breakfast the next morning, and she said she had to return some stuff at the mall and asked if I wanted to come. I said sure.
While she was returning clothes, I found a sick Patagonia jacket. She saw me checking it out and asked if I wanted it. It was like two-fifty. She took it off the rack and went to the counter.
I thought she was just committed to the bit until she pulled out a manila folder stuffed with hundred-dollar bills. My jaw dropped. She winked. I asked her about the money, and she just said not to worry.
I knew she worked a near-minimum-wage job, so it was strange, but I let it go. She drove me home, and before I got out of the car she said hold on. She pulled out the folder again and threw six hundred dollars into my bag. I tried to give it back.
She said she had a bunch, opened her purse, and there were six or seven more folders just like it. I kept the money. Over the next few months she’d randomly send me a hundred to five hundred dollars on Venmo every week or so. She kept buying me things.
If I mentioned being hungry, she’d order pizza for me and my roommates. If I mentioned wanting something, it showed up in an Amazon box days later. On my next break I went home and we met up again. We skipped the sushi and went straight to the horizontal hokey-pokey.
She stayed the night, we watched a movie. The next morning she put ten hundreds on my coffee table. I knew she wouldn’t take no for an answer, so I took it and said thanks. She drove off, waved, everything seemed normal.
A few hours later I texted her. It didn’t go through. I tried Snapchat. She’d deleted or blocked me.
Every form of social media, gone. I played it cool, didn’t call a bunch. Then at two a. m.
one night I got a call from a blocked number. It was her. I asked what was going on, and she shushed me. She was whispering, but not in a sexy way.
She sounded serious, a little scared. She told me I couldn’t tell anyone about our interaction, her name, anything. She asked me to delete the pictures she’d sent me. I asked what the hell was going on.
She said she had to go and hung up. I never heard from her again. Still got the Patagonia though. At a dive bar on a Tuesday night, a woman came in wearing yoga pants and a tank top.
She was beautiful, looked like a hot suburban mom in her early forties. Turned out she was mid-divorce, had been moving out of her house all day. We got to chatting, exchanged numbers, and I went to her place later that night. The door opened and it was on, no introduction needed.
The next day she kept saying she couldn’t believe she was with such a younger guy. I look young for my age, so I assumed she just thought I was younger than I was. I told her I was thirty-three. She said that’s what she thought.
She was fifty-five. I was shocked, but also thought it was cool. For the next year we had an ongoing relationship. She never cared or got jealous about who I was dating.
We’d talk about sex with other people while we made love, which was hot because neither of us was possessive. She was adventurous, and I felt I could open up about anything without judgment. She always paid for restaurants, paid for us to take a week-long trip out of town. She talked about how an older man had set her up in business when she was young, and she wanted to do the same for me.
We planned that out. She even suggested I move into her spare bedroom and be roommates, saying she wouldn’t be jealous if I brought a girl home. I thought that was too complicated, so I declined. I moved away.
She found someone her own age, and we talk less and less. But I keep her updated on my life. I think of her fondly and often. I tell her I love her.
She’s a very special woman to me, and she still inspires me. This happened in Tokyo about five or six years ago. I met a client at work when I was twenty-six. She was thirty-two, really cute, very smart and educated.
We got on well. She had a lot of cute quirks. She was a train geek, which is rare for a woman in Japan. She could tell you the make and model of every pantograph on every train in operation.
I didn’t know who she was when we first met, but my boss later told me to treat her like a VIP at all times. Anyone who knows Japanese politics has heard her name. Our work project wrapped up, and we went out to eat. She said she needed help preparing for an interview at a famous company, for a unique role they’d essentially create just for her.
I said I’d help, genuinely, with no ulterior motives. We met up to prep, and after we finished she invited me to play darts. I’d never played. We went to a darts bar, and somehow we ended up playing a game where the loser drank tequila shots.
She mopped the floor with me, but we both kept doing shots until way past the last trains home. We wound up at an internet cafe until she got touchy-feely, and then we got a hotel together. That’s how our relationship began. She turned out to be richer than God.
She bought me all kinds of stuff, never let me pay for dates even though I was making good money. She wanted to take me on trips around Asia. She bought me nice watches and clothes, which I still have and cherish. She had a Benz and an Aston Martin and other cars just sitting in parking spaces in the middle of Tokyo.
I probably would have married her if not for complications with her marital status. I found out after a few weeks that she was in a terrible loveless marriage and had a young child. It made me uncomfortable at first, but I started to understand she was trapped. Due to societal pressure, she had no real way to divorce.
Neither of them wanted the marriage, both were seeing other people, but because of their high profile in Japanese media, a divorce was out of the question. We broke up when we realized that having a kid together would cause irreversible damage to her political career, and that divorcing to marry a white guy would end her professionally. That really sucked, but it was the truth. She was the best girlfriend I’ve ever had.
If I’d met her three years earlier, my life would be completely different now, and not for the money. I couldn’t care less about that. I’ve never met someone I connected with so well. She really was the one that got away.
Six years ago, just out of college in Southern California, living with my grandpa, I asked out a Chinese grad student I met at work. On our second date she picked me up in a shiny black Audi, said her parents leased it for her. We went to a Chinese restaurant. I’d paid on our first date and assumed I’d keep paying, because I was a red-blooded Korean American man, even though I made fifteen dollars an hour.
When she started ordering lobster, duck, and enough food to feed eight, I got nervous. The check came. I reached for it. She snatched it away, pulled out her wallet, and removed three hundred-dollar bills like it was nothing.
I caught a glimpse of the stack inside, all crisp and new, had to be at least two grand. She said she didn’t like going to the bank, so she got it all at once. She had more in her wallet than I had in my name. She paid for the two-hundred-plus-dollar meal and let me have the leftovers.
That fed me for a week. After that we alternated paying. My meals were cheap on Yelp. Hers were three-dollar-sign places.
She paid for Disneyland tickets, Lakers games, some fantastic meals. Then, five months later, she graduated, her student visa expired, and she went back to China. She was really down to earth. Once we went near downtown and she street-parked in Skid Row.
I advised against it, pointing at the homeless encampments. She said it was no big deal. Her English was good, but once we were lying in bed late at night and she said out of nowhere, “I’m funnier in Chinese. ” I thought it was hilarious and also kind of sad.
Maybe because of that, we didn’t text much outside of planning weekends. I sometimes wondered if she had two or three boyfriends she cycled through. She didn’t have Facebook, only Weibo. I texted her a few years ago.
The blue bubbles were green now. Still, we had a lot of fun, and she helped me get through those post-grad broke-ass blues. I hope she’s doing all right. I got a free personal training session at Equinox.
This woman working out there was on the same routine as me, so during the session we kept running into each other at the same benches and machines, joking about it. At the end of the session we chatted. She was super pretty and fit, forty-one, incredibly intelligent, with her own private practice doing sex therapy. We clicked.
I’m twenty-six. After my session the trainer let me stay and keep working out. The therapist came back over, and we exchanged numbers. No more than five replies into our first text conversation, she straight-up told me I was cute and that she was always busy, so she was looking for a casual hookup relationship with me.
I told her how convenient, I was in the same boat. She lives nearby, so I’ve been going to her place about once a week for the last two months just to have sex and hang out. She’s really into zodiac and tarot. She likes to analyze me and eventually wants to read my cards.
I don’t know, it’s a small price to pay. It’s actually pretty interesting, and sort of sexy when she talks about it. This wasn’t a sugar mama thing at first. But we started going out to dinner just for fun, and even though it wasn’t really dates, she paid for everything.
Then she started buying me nice things, nothing too personal, but nice bottles of wine, scotch, a candle she liked. Nice gift-type things. This week the gifts went a step further. She’s going to Barbados in February.
I jokingly said I’d love to go. She booked me a ticket because she felt like it. I’m an avid surfer, so she wants me to surf all morning while she sleeps, then basically bang her on different parts of the island. I’m dropping zero dollars.
She’s adamant about not having a relationship outside of a casual one, for numerous reasons. Having spent enough time with her, I think she’s genuine and I believe her. She definitely likes spending money on me, but not in frivolous ways, not like the clearer-cut sugar mamas. Still, I think the security is part of the appeal.
This one I got secondhand, but it fits the theme. We were lying in bed talking about our pasts, and a guy told me about a job he had right after high school, working at a corner store the summer before college. The owner had a car accident and became partially disabled. He asked the young man if he wanted to earn extra money working around his house while he recovered.
Things went well for about a month until one day the store owner was gone and his wife came up to the garage in an open bathrobe. At first he blushed and turned away. But after a week or so of her turning up half-naked in different spots around the house, he took her up on the offer. The owner suddenly doubled his salary at the store, but he only had to go there once a week.
The rest of the time he reported to the house, where his salary also doubled, and they bought him a used car. Except for his one day at the store, he never did any work except sexing the wife. He suddenly had enough to cover his tuition. He went to a local college and kept that job for two years.
The owner rehabbed, moving from wheelchair to crutches to a cane. One day he called the young man, sighed, and told him they were selling the house and the store and moving to Florida. The old man said, “I want you to know you saved my marriage. You think I didn’t know you were sleeping with her this whole time?
It was my idea. I love my wife and I’d do anything for her. That accident changed things for us. You’re young and just wanted some ass and a car and a few extra dollars for school.
An older man would have come in here and had the house and the store and my wife too. We’re moving on, but you don’t have to worry about tuition. Just keep on with school. ”
His tuition stayed paid until he graduated.
He never saw the old man or his wife again. I’m currently in a friends-with-benefits thing with an older woman. I’m twenty-three. She’s thirty-seven.
There’s a sugar mama element to it, mostly that she buys me nice dinners and drinks, and I give her a good time in bed and playing Switch. We met on Bumble. She says she wasn’t originally looking at guys my age, but her friend messed with the age filter without telling her, and she matched with me anyway. She’s a professor and researcher.
I’m a grad student, not her student, but in a similar field at the same university. She didn’t realize I was that much younger until we’d already been texting for a while and had a date planned. She went through with it anyway. The sexual tension was there from the start.
I was nervous the first time, but she has some dominant tendencies, especially in bed, so I think she found it cute. We had sex four times that night and haven’t slowed down much since. We aren’t exclusive. She goes out with guys her age.
I hang out with girls my age. She actually encourages it. She even likes hearing me talk about whenever I get laid with a younger girl. It’s a crazy whirlwind, especially since I was a virgin less than a year ago.
But it’s fun. I’d highly recommend it, although I feel like if I ever get famous or run for office, it’s going to come out somehow and scandalize my entire extended family to death.